Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines

Abstract Base-induced cyclization of active methylene isocyanides with carbamimidothioates for the synthesis of N,1-aryl-4-tosyl/ethylcarboxy-1H-imidazol-5-amines is reported. The diversity of the reactions is exemplified by using various carbamimidothioates obtained from symmetrical N,N-disubstitut...

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Main Authors:	Dukanya Dukanya, Toreshettahally R. Swaroop, Shobith Rangappa, Kanchugarakoppal S. Rangappa, Basappa Basappa
Format:	Article
Language:	English
Published:	Georg Thieme Verlag KG 2019-07-01
Series:	SynOpen
Subjects:	imidazoles isocyanides cyclization carbamimidothioate oxazole
Online Access:	http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690328

id	doaj-4a8e862d6d714d168142f96ebe52e2ac
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spelling	doaj-4a8e862d6d714d168142f96ebe52e2ac2020-11-25T03:18:43ZengGeorg Thieme Verlag KGSynOpen2509-93962019-07-010303717610.1055/s-0039-1690328Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-aminesDukanya Dukanya0Toreshettahally R. Swaroop1Shobith Rangappa2Kanchugarakoppal S. Rangappa3Basappa Basappa4Department of Studies in Organic Chemistry, University of MysoreDepartment of Studies in Organic Chemistry, University of MysoreAdichunchangiri Institute for Molecular MedicineDepartment of Studies in Chemistry, University of MysoreDepartment of Studies in Organic Chemistry, University of MysoreAbstract Base-induced cyclization of active methylene isocyanides with carbamimidothioates for the synthesis of N,1-aryl-4-tosyl/ethylcarboxy-1H-imidazol-5-amines is reported. The diversity of the reactions is exemplified by using various carbamimidothioates obtained from symmetrical N,N-disubstituted, unsymmetrical N,N,N-trisubstituted, and unsymmetrical N,N-disubstituted thioureas. This diversity is further enriched by different isocyanides. A mechanism for the formation of the title compounds is proposed.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690328imidazolesisocyanidescyclizationcarbamimidothioateoxazole
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Dukanya Dukanya Toreshettahally R. Swaroop Shobith Rangappa Kanchugarakoppal S. Rangappa Basappa Basappa
spellingShingle	Dukanya Dukanya Toreshettahally R. Swaroop Shobith Rangappa Kanchugarakoppal S. Rangappa Basappa Basappa Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines SynOpen imidazoles isocyanides cyclization carbamimidothioate oxazole
author_facet	Dukanya Dukanya Toreshettahally R. Swaroop Shobith Rangappa Kanchugarakoppal S. Rangappa Basappa Basappa
author_sort	Dukanya Dukanya
title	Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines
title_short	Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines
title_full	Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines
title_fullStr	Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines
title_full_unstemmed	Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines
title_sort	cyclization of activated methylene isocyanides with methyl n(n),n′-di(tri)substituted carbamimidothioate: a novel entry for the synthesis of n,1-aryl-4-tosyl/ethoxycarbonyl-1h-imidazol-5-amines
publisher	Georg Thieme Verlag KG
series	SynOpen
issn	2509-9396
publishDate	2019-07-01
description	Abstract Base-induced cyclization of active methylene isocyanides with carbamimidothioates for the synthesis of N,1-aryl-4-tosyl/ethylcarboxy-1H-imidazol-5-amines is reported. The diversity of the reactions is exemplified by using various carbamimidothioates obtained from symmetrical N,N-disubstituted, unsymmetrical N,N,N-trisubstituted, and unsymmetrical N,N-disubstituted thioureas. This diversity is further enriched by different isocyanides. A mechanism for the formation of the title compounds is proposed.
topic	imidazoles isocyanides cyclization carbamimidothioate oxazole
url	http://www.thieme-connect.de/DOI/DOI?10.1055/s-0039-1690328
work_keys_str_mv	AT dukanyadukanya cyclizationofactivatedmethyleneisocyanideswithmethylnnnditrisubstitutedcarbamimidothioateanovelentryforthesynthesisofn1aryl4tosylethoxycarbonyl1himidazol5amines AT toreshettahallyrswaroop cyclizationofactivatedmethyleneisocyanideswithmethylnnnditrisubstitutedcarbamimidothioateanovelentryforthesynthesisofn1aryl4tosylethoxycarbonyl1himidazol5amines AT shobithrangappa cyclizationofactivatedmethyleneisocyanideswithmethylnnnditrisubstitutedcarbamimidothioateanovelentryforthesynthesisofn1aryl4tosylethoxycarbonyl1himidazol5amines AT kanchugarakoppalsrangappa cyclizationofactivatedmethyleneisocyanideswithmethylnnnditrisubstitutedcarbamimidothioateanovelentryforthesynthesisofn1aryl4tosylethoxycarbonyl1himidazol5amines AT basappabasappa cyclizationofactivatedmethyleneisocyanideswithmethylnnnditrisubstitutedcarbamimidothioateanovelentryforthesynthesisofn1aryl4tosylethoxycarbonyl1himidazol5amines
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Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines

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